


Winn Gets Pegged

by steviejoel69



Category: DC Extended Universe, DC Super Hero Girls (Cartoon 2019), DC's Legends of Tomorrow (TV), DCU (Comics), Shazam! (2019), Supergirl (Comics), Supergirl (TV 2015), Supergirl (TV 2015) RPF, The Flash (TV 2014)
Genre: Alien Fetish, Cougar - Freeform, F/M, Jeremy Jordan - Freeform, M/M, Multi, PERIODT, Tentacle Porn, Threesome, age gap, anal fissures, find out which ones, half of these are fake, horny on main, jeremy jordan has a nine inch penis, miku hatsune - Freeform, pisss kink, romantic slowburn, thirsty for shredded aliens, twink pegging, two dicks one hole, two dicks one twink, winn fucking dies
Language: English
Status: In-Progress
Published: 2019-09-08
Updated: 2019-09-08
Packaged: 2020-10-12 07:16:23
Rating: Not Rated
Warnings: Major Character Death
Chapters: 1
Words: 2,094
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20560361
Author URL: https://archiveofourown.org/users/steviejoel69/pseuds/steviejoel69
Summary: After Winn has his heart broken by Kara, he finds a way to cope.





	Winn Gets Pegged

It had been a month since Winn had been rejected by Kara. He had kind of gotten over her. At least for the most part. His asshole, however, was still lonely and tight. He needed a release. Not to say he was a virgin, because nerds fucked. They definitely fucked. Just not in the way normal people do. The last time he got some was last year at Crunchyroll Expo, when he was rawed by a guy dressed as Hatsune Miku in a smelly-ass stall near a toilet full of piss, and he only lasted three minutes.  
The guy needed some, and he needed it now.  
Winn wasn’t one to beg for sex, but he had really been relying on landing it with Kara to satisfy his needs. But, alas, shredded alien chicks just don’t lust for short, pasty, IT guys :/. And sadly, the typical human population didn’t either. But Winn was determined to fuck. And fuck hard. He needed some dick or pussy immediaTeLY. Or both. Preferably at the same time. He was horny, and he was horny NOW. So he hacked into the DEO firewall, turned the administrative website restrictions off, and went into incognito mode, just incase, to put out a flier on craigslist asking for someone, preferably an alien, to top him for 20 cents (which he found at the bottom of Alex’s drawer, before being decked across the room for looking through her personals.)  
Winn had to act quickly, before the DEO caught onto him, So the flyer had its fair share of spelling mistakes, but it got the point across. He sent it into the world and went back to business as usual. In all honesty, he didn’t care if the DEO found out, he would just go somewhere else like back to CatCo or literally anywhere. He was pretty sure Hank and the rest of the DEO knew that too, but he didn’t want the company to get in trouble. He deemed himself a pretty considerate guy. Why didn’t Kara see that? :( Oh well. He’ll just go and cry in the bathroom during his break. Again.  
When he came to work the next day, it was business as usual. It wasn’t until kara awkwardly approached him and said, “Winn? Hank wants to see you in his office,”in that overly sweet and enthusiastic voice she had taken to using since she broke his heart into a million pieces. He sighed, not turning around to face her.  
“Okay. Tell him I’ll be right there.” He still couldn’t seem to fake a good, happy voice yet. When she walked away, he stood up and forced his legs to move in the direction of Hank’s office. To be honest, Winn had forgotten all about his cry for sex. Today was rainy and dismal, it was more of a mope-around-in-depression day, rather than a ‘be rampantly horny’ day. So when he walked in, the last thing he was expecting was for Hank to hand him his flier, printed onto a piece of paper.  
There was a moment of awkward silence.  
“You ready?”  
All of the blood drained from Winns face, and his knees went weak. (AN: I think we know where it all went ;))  
“Well, are we fuckin’ or not?” Hank said impatiently.  
“B-but you’re not an alien…” Winn managed to squeak out. In that moment, all of Hanks skin started to peel off, revealing the sexiest, greenest alien Winn had ever laid eyes on.  
“Oh, God it’s just like the hentai… A Martian Manhunter in the flesh…” Winn was breathless.  
Hank smirked at his child-like wonder, “Are we gonna fuck or not? I don’t have all day you know.” Hank moved toward Winn from behind and caressed Winn’s succulent hips. He rested his chin on Winn’s trembling shoulder and pressed his green face against Winns baby face. Winn could feel his rough reptilian skin rasp against his acne scarred cheek. The martians green lips moved seductively to form the sentence “I’m a very busy martian…” His arms moved up and cradled Winn’s fagot titties, then moved downward and began to unbutton the plaid shirt Winn was wearing, which he had worn every day this week. Winn whimpered at the cold, inhuman touch of J’onn’s reptilian hands. This made J’onn even hornier. He unbuttoned with haste and Winn groaned softly.  
“Patience is a virtue young one, you need to be taught a lesson.” And with that, J’onn took the collar of Winns shirt and forced him to bend over. HIs hands snaked toward his belt and tenderly unfastened it.  
They were lost in lust’s embrace. Winn was moaning with pleasure as J’onn showed him how they do it on Mars. Suddenly, the door to Hank’s office swung open.  
“Mr. Henshaw! I received your-” a tall, dorky looking man wearing glasses walked into the room, but stopped upon seeing what was going on on the floor, “Oh… is this a bad time, J’onn…” The man faltered. His face was burning bright red, he looked a little upset.  
Winn looked up mid-climax. He felt J’onn twist his abdomen around to face the newcomer. “You didn't lock the door..?” Winn puttered out between labored breaths.  
“CLARK!” J’onn exclaimed.  
Winn yelped as the alien pulled out of him. “Who the fuck is Clark…?” Winn groaned. He relaxed his posture; J’onn stood up and approached the bespectacled man. Dick still out, mind you.  
“I see you have a type…” the man who went by Clark said, snidely.  
“Oh are you still on this?” J’onn responded in his defense, “You were the one who chose to follow Earth’s heteronormative ways and marry Lois Lane!” The martian began to raise his voice.  
“I had no choice, J’onn! You were a giant green alien! I couldn’t put pictures of you on my desk!”  
“I am a shape-shifter! That is literally my superpower!”  
“But you refused to shapeshift into a woman!”  
“It was time Clark! The world needed a gay superhero and you know it!”  
“It was the 50’s J’onn! I would have been lynched and then when I wouldn’t have died, I would be experimented on!”  
While this shouting match was happening, WInn just sat on the floor, watching as if it were a ping pong game. What had he gotten himself into? Why was his boss an alien from Mars, and why couldn’t this Clark guy die? Why did he post that flyer?  
Winn was snapped out of this train of thought when all of the shouting suddenly stopped and Clark had pushed J’onn up against his own desk. J’onn’s hands moved up to caress Clarks face as they made out, and while doing, Clark’s glasses were pushed up onto his head.  
“HOLY SHIT IT’S SUPERMAN!” Winn screamed. The couple snapped out of the hypnotic spell they had been under and whipped around simultaneously, remembering that Winn was in the room. The two aliens walked toward Winn, smirking as they exchanged glances.  
Clark grabed Winn by the hips and rolled him onto his back forcefully. “Fu-,” he muttered.  
“Keep quiet,” J’onn said with force. Winn couldn't help his raging hard-on. He had always wanted to be plugged from both ends. The anticipation ate away at Winn as Clark teasingly unbuttoned his pants.  
“Your thirsty little flyer spelled it all out. You want to be tied up and paralyzed from being pounded into oblivion.”  
A sudden wave of confusion washed over Winn. He didn’t remember mentioning ropes. Of course he wanted it, but he was too embarrassed to add that to his flyer. He thought that might scare away any potential takers. But that wasn't the case…  
As J’onn tied up each and every one of Winn’s limbs, Clark got to work. He began to massage Winn’s bulge over his underwear. “Impressive,” Clark muttered, “but just wait until you see mine.”  
Winn’s mind was racing. He took pride in being abnormally large (A fact that he mentioned to Kara, but she didn’t want his 9 inch penis in her wet…)  
The following day at CatCo was absolute hell. Winn was late because he literally could not move without excruciating pain. He might need to see a doctor after last night. As he limped across the rows upon rows of desks to finally reach his, at the other side, he could feel the tender skin of his nether areas ripping again. Winn tried with all of his might to keep a straight face but apparently it wasn’t enough because when his boss Cat Grant came sauntering in her head snapped immediately in Winn’s direction.  
With a cold, almost skeletal hand, she moved her sunglasses down her nose. “Will. In my office. Immediately.” Cat demanded. Winn went cold. Oh God. This was it. She was going to kill him. Finally, after five years of loyal service she had finally come to end his misery. “Y-yes Ms. Grant!” He stammered and stood up quickly. Which he regretted. He limped over to her office as quickly as his pain tolerance would let him. He entered her glass palace and felt its twenty television screens boring down into his soul. Nope, that was just Ms. Grants eyes.  
“Winston... “ Ms. Grant said as she turned around in her wheely chair to meet Winns terrified gaze. Winn burst into tears.  
“No crying in my office Mr. Scott!” she snapped her fingers, eyes blazing, “dry up, you’re not in trouble… you millennials and your crippling anxiety…” Ms. Grant said with disgust. She stood up and strutted toward Winn’s pathetic, sniveling form. She bent down and reached into a drawer in her desk, rummaging around until her eyes spotted what she was looking for. Winn watched as his boss pulled out the most expensive looking strap on he had ever seen in his whole life. The purple strap on turned pink where her fingers were.  
\  
“W-What's that?” Winn wheezed, choking on his own saliva.  
“Please Whit, you’re a smart boy, you know what this is.” She shifted her weight as she tossed it from hand to hand.  
“W-what are you gonna do with it?” His voice trailed off as he glanced behind him at the (very transparent) glass wall of her office.  
“I think you know..” She flashed a malicious grin of perfect teeth and Winn shuddered.  
She reached out and brushed a perfectly manicured finger under his jawline, digging in when she got to where the soft fleshy part meets the cartilage of the chin and she dragged him closer so their eyes met. Winn actually had to bend down a bit to look the older woman in the eye directly and he was kind of into it. This must have shown, because Ms. Grant frowned and rolled her eyes. He liked that too. A lot. Without warning, a bulge began to rise in the groin of his pants, making itself known against Cat's pencil skirt. “Don’t get cocky, dweeb,” She yanked on his tie dragging him down and she pushed his head down. “Get on your knees.” Winn begrudgingly obliged. Cat lifted her leg and pushed Winn onto his back,the tip of her stiletto heel digging into his sternum.  
She got on top of him and immediately began undressing, starting with his shirt and progressing downward. Once Winn was properly naked, Cat flipped him over and traced her acrylic nails down his back, landing around his bruised hips. “Looks like I’m not the first person here…” She whispered in his ear. Winn just whined in response. Cat wrapped her strap around her waist, over her work attire, and her hips pushed forward, thrusting into him. Winn screamed in agony. “Quiet Winston, you don’t want to attract attention.” Tears. So many tears. Winn was a sobbing mess. The whole ordeal didn’t last much longer. Although his tears and pain turned Cat on at first, after a while his insufferable sobbing became taxing to her and she stopped halfway through.  
“I thought you wanted this… do you always cry during sex?” Cat asked as she took the strap on off. Winn shuddered a sigh. “I thought you were stronger than that.” Cat said as she cleaned the strap on off and placed it back in her desk. Winn collapsed in defeat. Cat shook her head in disappointment.  
“Don’t just stare at me, naked on the floor! Get dressed, and go figure out the weather or whatever your job is.”  
Winn tried to get up but he felt his mind fleeting and everything got suddenly dizzy. He blacked out.

Winn had learned his lesson.

Carol got the strap

**Author's Note:**

> dicks out for clark kent


End file.
